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Abstract

Electronic devices based on organic materials have been an area of intense research for the past several years. Pentacene,
an oligoacene, is regarded as a benchmark due to its high charge carrier mobility. However it has poor solubilty, unoptimized
π-overlap and is highly unstable. We have successfully demonstrated that peri-functionalization with
trialkylsilyl ethynyl groups enhances the π-stacking, solubility and stability of pentacene and related compounds. TIPS
pentacene exhibits both two dimensional (2D) π-stacking and good solubilty in common organic solvents. However
changing the solubilizing groups or functionalizing the acene core results in a disruption of the desired 2D π-stacking.
Molecules with one dimensional (1D) π-stacking have poorer mobility than those with 2D π-stacking and hence larger
solubilizing groups are required to change the π-stacking to 2D. The emphasis of this paper is to show how small
changes in substitution can disrupt π-stacking in these molecules and how one can achieve the desired π-stacking by
careful selection of solubilzing groups.

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Journal of Applied Remote SensingJournal of Astronomical Telescopes Instruments and SystemsJournal of Biomedical OpticsJournal of Electronic ImagingJournal of Medical ImagingJournal of Micro/Nanolithography, MEMS, and MOEMSJournal of NanophotonicsJournal of Photonics for EnergyNeurophotonicsOptical EngineeringSPIE Reviews